Image by Gerd Altmann from Pixabay

How I Learned To Be The Boss

Working Freelance Was Different Than Expected

Dena Warfield
Live Your Life On Purpose
4 min readJan 18, 2019

Freelance Job #1

After a forced retirement from an illness which involved multiple surgeries, I decided to go back to work. The Freelance market was like a neon sign flashing in my eyes,

“Work Here”, “Work Here.” I gave it a try.

With my years of experience, I landed an interview, I think, the second or third proposal I sent out. Excited!

On the Skype, call questions bombarded me about my experience, my qualifications — “Had I ever worked remote before”, “Was I experienced with Team, Slack, Outlook”, “Could I manage a virtual office?”

A virtual office? I’ve always worked on computers doing data entry, programming, an office manager — yes. But a virtual office? What the heck did a virtual office look like?

“Yes, I can handle it” — my standard response. I knew I could figure it out. I just hoped I could figure it all out sooner rather than later.

The job was offered to me and I accepted with trepidation. “I can always figure things out,” I kept telling myself.

Then the “boss” on the other end of Skype told me his story. He told how he had worked for several big corporations, naming off the companies, and how he had been fired from each one.

Red flags began waving in my mind as he relayed his story, “Fired, why?”

“If he’s been fired from all these high-level companies, what kind of a boss is the going to be?”

“Should I take the job?”

“Oh, it can’t be that bad, could it?”

Long story short, I took the job. I loved the variety. I received a myriad of jobs, data mining, writing, maintaining websites, transcribing videos into text, loved the work.

We’d Skype every few days. He was fun. Then the other shoe dropped. Extra space in a document caused an explosion. “You’re taking too much time on that transcription,” even though it was perfect.

“Send me what you have completed, NOW,” the growl came over email.

I began pulling back from the intense tension and stress.



Dena Warfield
Live Your Life On Purpose

Writing about ADHD from a non-ADHD perspective. Using a MA in Human Behavior and personal experience. Illustrated by fictionalized stories.